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3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties

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Abstract

A series of twelve 3-piperazinyl propenylidene indolone merocyanines was synthesized in a one-pot fashion using a consecutive three-component insertion-coupling-Michael addition sequence. Physical-organic treatment of the absorption data of a consanguineous series of this library allows semiquantitative Linear Free Energy Relationships (LFERs) to be established and confirmation of the positive absorption solvatochromicity. All Boc-substituted piperazinyl merocyanines display aggregation induced emission (AIE), which was corroborated for two solvent systems. In particular, crystallization-induced emission enhancement (CIEE) induced by ultrasonication could be shown for a model chromophore by confocal laser scanning microscopy (CLSM).

Graphical abstract: 3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties

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Publication details

The article was received on 04 May 2017, accepted on 02 Jun 2017 and first published on 08 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QM00198C
Citation: Mater. Chem. Front., 2017, Advance Article
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    3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties

    M. Denißen, N. Nirmalananthan, T. Behnke, K. Hoffmann, U. Resch-Genger and T. J. J. Müller, Mater. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QM00198C

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